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Pensacola Beach Vacation Rentals with Private Pool

(41 rentals)
Pensacola Beach Condo
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Pensacola Beach Luxury Location | Blue Angels Beachfront Views | Indoor & Outdoor Pools | Resort Style Amenities | Aqua Spa On-SiteExperience coastal luxury at Beach Club Resort & Spa condo 1502, proudly managed by Beach Getaways, where breathtaking panoramic views of the Florida Gulf Coast...

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$294
avg per night
Pensacola Beach Townhome
Sleeps 15, 4 bedrooms, 3 bathrooms
22 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This 4.5 bedroom 3 bath townhome with garage is in the gated, low density complex of Regency Cabanas.Ground level includes a private three car garage equipped with a ping pong table, beach and pool toys, lounge chairs, and umbrellas and cart.Bright and inviting, the living, dining and kitchen...

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Featured review

"Perfect for Family Gathering"

This rental was terrific! Our large family had no problem staying in this spacious and comfortable cabana. The kitchen was well stocked, plenty of beach supplies, and the whole place was well maintained....

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$300
avg per night
Pensacola Beach House
Sleeps 17, 6 bedrooms, 4.5 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to 703 Ariola Drive, your dream getaway on beautiful Pensacola Beach. Just 45 steps to the beach access, this 6-bedrooms, 4.5-baths home combines modern coastal style, comfort, convenience and perfect for families and groups. Property is owned and operated by the owner (Kim), no middle man.HIGHLIGHTS: ...

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Featured review

"Excellent property and condo"

The property is beautiful and very well maintained. The beach is a bit thin but sand is fantastic and facilities are very nice with lots to do on property. The unit itself was fantastic. Only issue was...

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$861
avg per night
New
Pensacola Beach House
Sleeps 16, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Is it time to get away from the hustle and bustle of it all? This is the place for you! Pensacola Beach is a lovely beach environment without the overcrowding typical of other Gulf coast beaches and has a little something for everyone. There is plenty to do on the beach and at the several restaurants,...

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Pensacola Beach Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This Spacious 2-Level, 2-Bedroom, Condo is located in a 14-Acre PRIVATE RESORT on a Beautiful Island with direct access to both (2) Gulf Beaches, Great Water Views, Huge Olympic-Size Pool, 2 1/2 Baths, Sleeper Sofa, Private Fishing Pier, Parking directly in front of Townhome, Easy On/Off Island Access,...

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Featured review

"Relaxing By The Sound"

We enjoyed our stay at this quiet retreat. It is a large complex but very quiet. The unit has all the comforts of home. Bring a paddle board or kayak and enjoy! The gulf is across the street with easy access....

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$182
avg per night

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Pensacola Beach House
Sleeps 22, 6 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Signature Amenities of This Resort-Style Home:* Unobstructed Gulf Views - Steps to County Beach Access* Private Lagoon-Style Pool + Tiki Bar + Lounge Seating* Game Room with Pool Table, Ping Pong, Foosball and Basketball Game* 6 Bedrooms + Bonus Loft Area - Sleeps Large Groups Comfortably*...

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Featured review

"Anne's Island Girl"

The location was great. Beach right across the street. The house was beautiful and had everything you needed. We loved hanging out in the pool. We enjoyed the house. we'll visit again. Thank you for a...

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$773
avg per night
Pensacola Beach House
Sleeps 18, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Signature Amenities of this Private Gulf Retreat:* Gulf-View Luxury Home – Sleeps 18* One of the Largest Private Pools on Pensacola Beach* Rooftop Deck with 360° Views + Hot Tub Access* Chef’s Kitchen with Oversized Island + Double Refrigerators* Soaring Ceilings +...

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$659
avg per night
Pensacola Beach House
Sleeps 25, 7 bedrooms, 4.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of The Beach House:* Large private pool with patio seating, grill, and tropical landscaping* Deeded beach access just steps away on scenic Ariola Drive* Fully renovated interior with new furnishings, décor, and upgraded kitchen* Custom-built bunk room + separate...

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Featured review

"Beautiful and Spacious for our family!"

We love the decor! We have enough room for the whole family and we where right across the beach! The concierge text was always at our service! My favorite vacation home!

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$729
avg per night
Pensacola Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Special Offer for Extended Stays (Nov-Feb):Enjoy automatic discounts on stays of 28-30 days for the months of November through February! The longer you stay, the more you save—no need for extra codes or hassle. Book now to take advantage of our special extended-stay pricing and experience the...

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$175
avg per night
Pensacola Beach House
Sleeps 22, 6 bedrooms, 6 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of This Luxe Coastal Estate:* Gulf-View Luxury Home – Sleeps 22* Private Pool with Sundeck + Outdoor Shower* Elevator Access from Ground to 3rd Floor* Designer Interiors with Upscale Furnishings* Chef’s Kitchen + Indoor & Outdoor Dining*...

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Featured review

"Family vacation"

This house was AWESOME! Debbie was great. We got lost in find the house and she came out and helped find it, helped us in and let me know to contact her if we needed anything else. The house had everything...

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$830
avg per night
Pensacola Beach House
Sleeps 18, 6 bedrooms, 6.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of Tuscan Sun:* Gulf views from multiple rooms and decks* Elevator access to all levels* Private 18’ x 12’ pool with optional heat* Game room with pool table, wet bar, and queen sleeper sofa* Sleeps up to 18 with bunk space and flexible sleeping zones*...

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$876
avg per night
Pensacola Beach House
Sleeps 30, 8 bedrooms, 10 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of This Luxe Gulf-View Estate:* Rooftop Deck with Gulf Views + Game Room* Private 36-Foot Pool + Optional Heat* Elevator Access to All Floors* Gourmet Kitchen with Double Refrigerators* Two Living Rooms + Two Laundry Rooms* Professionally Designed Interiors*...

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$1,058
avg per night
Pensacola Beach House
Sleeps 15, 5 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

New Updates for 2025: New pool loungers, new balcony furniture off primary bedroom, outdoor dining table off kitchen, top floor balcony sectional, and rooftop area with new chairs!!Welcome to your dream beach getaway at Paradise Palms! Nestled in the heart of Pensacola Beach, our stunning 5 BD | 6...

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$526
avg per night
Pensacola Beach House
Sleeps 16, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Signature Amenities of The Sunshine House:* Private pool with shaded lounge space + poolside bathroom* Direct beach access via private path to the shoreline* Gulf views from both floors and multiple decks* Event-friendly with romantic string-lit lower patio* Spacious chef’s kitchen...

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Featured review

"Great group vacation home"

This house was perfect! I came here for spring break. A minute walk to the beach, 5 minute drive to the boardwalk, and the house was so comfortable! Not cramped at all, even with 14 adults. If I plan on...

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$543
avg per night
Pensacola Beach House
Sleeps 22, 7 bedrooms, 6 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of This Spacious Coastal Home:* Prime Location on Ariola Drive - Steps to the Gulf* Private Pool + Expansive Deck with Outdoor Dining + Loungers* 7 Bedrooms + Bunk Room - Sleeps Large Families and Groups* Gulf Views from Oversized Covered Porch + Deck* Cowley Park...

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Featured review

"911 Ariola on Pensacola Beach"

This 7br was prefect for our family of 14 over Thanksgiving. The 2 refrigerators and 2 dishwashers in the kitchen helped me feed our group. The kitchen is well stocked with ample pots, pans, dishes, cups,...

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$757
avg per night
Pensacola Beach House
Sleeps 20, 6 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Signature Amenities of this Luxury Home:* Gulf + Sound Views from Rooftop Deck* Private Heated Pool with Lounge Deck* Chef’s Kitchen + Butler’s Pantry with Beverage Station* Screened Outdoor Living Room with Fireplace* Game Room with Ping Pong, Foosball + Cornhole*...

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$855
avg per night
Pensacola Beach House
Sleeps 30, 6 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Signature Amenities of this Beachfront Stunner:* Direct Beachfront with Private Walkway* Oversized Gulf-Front Decks + Panoramic Gulf & Sound Views* Private Swim Spa Overlooking the Water* Luxury Chef’s Kitchen + Executive Design Throughout* Game Room with Pool Table,...

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$1,079
avg per night
Pensacola Beach House
Sleeps 22, 6 bedrooms, 6.5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of The Great Escape:* Prime location on Ariola Drive with stunning Gulf views* Private pool with optional heating* Direct access to Cowley Park’s playground, track, and sports courts* Spacious one-level layout designed for large groups* Every bedroom has...

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Featured review

"Great Location"

This house was perfect for our multi-family beach vacation. We had plenty of room and privacy. The beach was just across the street and a decent size pool in the backyard. The kitchen had all the basics...

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$921
avg per night
Pensacola Beach House
Sleeps 12, 4 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

ATTENTION Winter Guests! Call us today for reduced monthly "snowbird" rates!Discover your dream getaway at "Sunny Daze" our stunning multi-story home that perfectly combines sophistication, relaxation, and coastal charm. Nestled just steps away from Avenida 17, a pristine public...

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Featured review

"Great summer location"

Sunny Daze house was a hit for the family on Pensacola Beach for the Blues week. It was dog friendly. The pool was a great asset, because the kids enjoyed that more than the sand at the beach. We will...

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$275
avg per night
Pensacola Beach House
Sleeps 14, 5 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Signature Amenities of Surf and City:* Sleek Modern Design with Gulf and Island Views* Balcony Pool Overlooking Beach and Commercial District* Elevator Access to All Levels* Game Room with Pool Table and Built-In Bunks* High-End Kitchen with Stainless Steel Appliances* Walkable...

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$620
avg per night
Pensacola Beach House
Sleeps 33, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Signature Amenities of Tranquility:* Brand-new game room with ping pong, foosball, and lounge space (added March 2025)* Sleeps up to 33 guests* Elevator access to all levels for convenience* Private 12’ x 26’ pool with optional heating* Direct beach access via private path...

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$635
avg per night
Pensacola Beach House
Sleeps 24, 7 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of The Sunshine Gulfside:* Private backyard pool with shaded and sunny lounging areas and optional heat***Please note that the owner has installed exterior cameras*** Three distinct sleeping zones - perfect for multiple families* Spacious deck with Gulf views and al...

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$721
avg per night
Pensacola Beach House
Sleeps 26, 7 bedrooms, 6.5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of This Luxury Estate:* Direct Beach Access + Expansive Gulf-Facing Decks* Private Pool with Sand Play Area, Lounge Seating + Gas Grill* Gourmet Chef’s Kitchen with Viking Appliances + 8-Burner Gas Stove* 2 Spacious Living Areas + Upstairs Wet Bar + Bonus Lounge...

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Featured review

"Great place to stay"

This house was clean and equipped with everything you need in the kitchen. The community was very friendly. It was a short walk to the beach. It has taken us longer to get to the beach staying in a condo...

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$952
avg per night
Pensacola Beach House
Sleeps 22, 6 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of This Spacious Gulf Retreat:* Ariola Drive Location with Unrestricted Gulf Views* Steps to Beach Access – Just Across the Driveway* Private Pool with Optional Heat ($80/day)* Expansive Gulf-Side Deck with Dining + Lounge Space* Two Living Areas – Perfect...

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Featured review

"Turkey Trip 2021"

This whole process was easy and stress free, the house was beautiful and spacious a short walk to the beach me and my family took advantage of every inch the property and the area we will definitely be...

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$713
avg per night
Pensacola Beach House
Sleeps 34, 6 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Signature Amenities of Palm Palace:* Brand-New Ground Floor Game Room + Living Space (Added 2025)* Private Pool with Optional Heat + Polywood Lounge Seating* Chef’s Designer Kitchen + Spacious Open Living Area* Elevator Access to All Living Levels* Just a 3-Minute Walk to the...

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$676
avg per night
Pensacola Beach House
Sleeps 23, 6 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Signature Amenities of The Beach Celebration:* Private Pool with Canal Views (One of the Largest on the Island)* Newly Renovated with Professional Coastal Decor* Game Room with Pool Table, Foosball, Darts + Lounge Area* Canal-Front Backyard with Fishing Access* Steps from Peg Leg Pete’s...

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$710
avg per night
Pensacola Beach House
Sleeps 23, 6 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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$1,057
avg per night
Pensacola Beach House
Sleeps 19, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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$707
avg per night
Pensacola Beach House
Sleeps 11, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you...

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Featured review

"Splendid"

Best vacation house ever. Plenty of room for both privacy and family time! Perfect location for a family vacation. BEACH was not crowded.

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$577
avg per night
Pensacola Beach House
Sleeps 16, 5 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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$710
avg per night
Pensacola Beach House
Sleeps 10, 5 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach HomesPlease note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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$1,386
avg per night
Pensacola Beach House
Sleeps 18, 5 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you...

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$986
avg per night
Pensacola Beach House
Sleeps 21, 5 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

View all property information

$586
avg per night
Pensacola Beach House
Sleeps 22, 7 bedrooms, 5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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Featured review

"Staycation with the Mermaid"

Perfect home for our family to chill and hang on the beach. We're locals and just wanted to have the beach scene part of our get together. Thank you for supplying all the amenities we expected.

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$812
avg per night
Pensacola Beach House
Sleeps 18, 5 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach HomesPlease note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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$793
avg per night
Pensacola Beach House
Sleeps 13, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach HomesPlease note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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Featured review

"Perfect!"

This condo has it all! Absolutely beautiful place and perfect location. The condo was well stocked with everything we needed. We will definitely stay here again.

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$475
avg per night
Pensacola Beach House
Sleeps 29, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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$1,689
avg per night
Pensacola Beach Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
10 reviews

Distance to beach: 40 yards to Pensacola Beach - Gulf of Mexico

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our PENSACOLA BEACH FRONT 'Home Away From Home'. Come enjoy a week at the beach, in our BEAUTIFUL PROFESSIONALLY DECORATED Home. 3 BR's, 2 BA's (sleeps 8 comfortably). Private and gated parking lot. Master BR(King), 2nd BR (Queen), 3rd BR(Queen, 1 Bunk),ON THE BEACH, END...

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Featured review

"Host was great to work with and unit had great views"

Kim was great to work with and made our stay easy. She registered our vehicles so we had an easier check-in. Being an east corner unit it has great views on two walls. Unit was as described, well maintained...

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$378
avg per night
Pensacola Beach House
Sleeps 17, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you...

View all property information

$608
avg per night
Pensacola Beach House
Sleeps 12, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach Homes.Please note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

View all property information

$370
avg per night
Pensacola Beach House
Sleeps 25, 4 bedrooms, 4 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Calendars will not update. Please visit our website for accurate calendar dates. Google Paradise Beach HomesPlease note that rates and minimum stay requirements change often and may be lower than what is displayed. For the most accurate pricing, please contact us directly. We want to offer you the...

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Featured review

"Family Reunion"

This home was an excellent place for us to gather together for a week. We met up with most of our kids and grandkids. The home was very well stocked for our group of nineteen. Each family had their own...

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$386
avg per night
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